ITunes Won't sync video or music anymore

I made my first aftere effects (adobe) movie, rendered it and converted to mp4.  It plays fine in iTunes but it just won't sync with my iPod (and yes i clicked advanced, make iPod copy).  It has also just started doing this with music to.  Please help because i need to put a very important music file (the beep test for school) on my iPod and would like to put my movie on there also. 
Specs:
Win7
iTunes 10.5
iPod 2g with iOS 4.2.1
If this isn't solved I will  never use another Apple product again.  I hate using iTunes as the only proper way to put stuff on an iDevice.  iTunes is always so glitchy and so slow.  I don't know why apple can't just make it to be able to put music/videos/photos on it just like any other mp3/mp4 player?

I am having the same problem. I had Season 1, 2, and some of 3 of Desperates Housewives, and music videos, and games all purchased from Itunes, on my Ipod. One day I plugged my Ipod up to Sync my newly downloaded shows, and it erased ALL of my music videos and TV shows and games. I have checked the settings and they are all correct. Can someone please please help me?
(My Itunes didn't work for 3 weeks, I had to reinstall Itunes and Quicktime, maybe this is part of my problem now. All of my music transferred without any problem.

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